electrophilic addition reactions
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11 Terms
hydrohalogenation
-h, -x
HCl, HBr, HI
C+
markovnikov
no stereospecificity
radical addition of hbr
-br, -h
HBr, ROOR, hv
radical
anti-markovnikov
no stereospecificity
acid-catalyzed hydration
-h, -oh
h20 w/ cat Hx, H2SO4, or H3O+
C+
markovnikov
no stereospecificity
halogenation
-x, -x
br2, cl2
x+
no regioselecivity
anti stereospecificity
halohydrin
-x, -oh
(br2, cl2) w/ h2O
x+
markovnikov-like regioselectivity
anti stereospecificity
oxymercuration demercuration
-h, -oh
1) Hg(OAc)2, H2O. 2) NaBH4
x+
markovnikov
anti stereospecificity
anti-dihydroxylation
-oh, -oh
1) mCPBA. 2) H3O+
x+
no regioselectivity
anti stereospecificity
hydroboration oxidation
-oh, -h
1) BH3, THF. 2) H2O2, NaOH
concerted
anti-markovnikov
syn stereospecificity
syn-dihydroxylation
-oh, -oh
1) KMnO4 or OsO4. 2) H2O
concerted
no regioselectivity
syn stereospecificity
ozonolysis
cleaves double bond and gives both carbons a carbonyl
1) O3. 2) SMe2
concerted
no regioselectivity
no stereospecificity
hydrogenation
-h, -h
H2 (g) and Pt, Ni, or Pd/C
concerted
no regioselectivity
syn stereospecificity
Note 
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